European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 19

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.065

ISI Journal Citation Reports © Ranking: 2014: 13/57 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

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  1. 1 - 100
  1. Full Papers

    1. Anion Transport

      Acyclic Pseudopeptidic Hosts as Molecular Receptors and Transporters for Anions

      Inés Martí, M. Isabel Burguete, Philip A. Gale and Santiago V. Luis

      Article first published online: 3 JUL 2015 | DOI: 10.1002/ejoc.201500390

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      Pseudopeptidic structures offer access to the design of efficient anion transmembrane carriers.

    2. Fluorinated Compounds

      A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one

      Denis N. Bazhin, Yulia S. Kudyakova, Gerd-Volker Röschenthaler, Yanina V. Burgart, Pavel A. Slepukhin, Maksim L. Isenov, Victor I. Saloutin and Valery N. Charushin

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500737

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      Reactions of the 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with N-binucleophiles are useful for the convenient preparation of trifluoromethyl-containing pyrazoles, pyrazolines, quinoxalines, isoxazoles, 1H-furo[2,3-d]imidazol-2(3H)-ones.

  2. Short Communications

    1. Mechanistic Organic Chemistry

      The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water

      Yi Wee Lim, Russell J. Hewitt and Brendan A. Burkett

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500637

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      An unprecedented rearrangement of 5-phenyl-1,4,2-oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.

  3. Corrections

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  4. Full Papers

    1. Natural Product Synthesis

      Synthesis of the C-8–C-24 Fragment of Maltepolide C by Using a Tandem Di­hydroxylation/SN2 Cyclization Sequence

      Debendra K. Mohapatra, D. Sai Reddy, G. Sudhakar Reddy and Jhillu S. Yadav

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500629

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      A highly stereoselective synthesis of the C-8–C-24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key step.

    2. Polyaromatics

      Synthesis of Annulated Anthracenes, Carb­azoles, and Thiophenes Involving Bradsher-Type Cyclodehydration or Cycli­zation–Reductive-Dehydration Reactions

      Settu Muhamad Rafiq, Ramakrishnan Sivasakthikumaran, Jayachandran Karunakaran and Arasambattu K. Mohanakrishnan

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500493

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      A conventional BF3·OEt2-mediated Bradsher-type cyclodehydration of 2-aryl/heteroaryl methyl benzaldehydes in CH2Cl2 at r.t. gave annulated arenes and heteroarenes in good yields. Alternatively, these anthracene analogues could be synthesized in better yields from the corresponding 2-aryl/heteroarylmethyl benzoic acids by Brønsted-acid-mediated cyclization followed by reductive dehydation.

  5. Short Communications

    1. Hypervalent Iodine

      Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryl­iodonium Salts

      Mekhman S. Yusubov, Dmitrii Yu. Svitich, Akira Yoshimura, Brent J. Kastern, Victor N. Nemykin and Viktor V. Zhdankin

      Article first published online: 2 JUL 2015 | DOI: 10.1002/ejoc.201500535

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      Aryliodonium salts bearing an extremely bulky, electron-donating triisopropylsilyl (TIPS) substituent in the phenyl ring are prepared and characterized by X-ray diffraction. Reactions of the TIPS-substituted arylodonium tosylate with bromide, azide, and thiocyanate anions predominantly afford products of nucleophilic substitution in the electron-rich aromatic ring bearing the TIPS substituent.

    2. Cu-Catalyzed Domino Reactions

      Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines

      Manna Huang, Dongting Huang, Xinhai Zhu and Yiqian Wan

      Article first published online: 1 JUL 2015 | DOI: 10.1002/ejoc.201500667

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      A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C–S and C–N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.

  6. Full Papers

    1. Sigmatropic Rearrangements

      Removable Silyl Group as a “Masked Proton” in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides

      Wenbo Mu, Yue Zou, Lijun Zhou, Quanrui Wang and Andreas Goeke

      Article first published online: 1 JUL 2015 | DOI: 10.1002/ejoc.201500654

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      In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). This protocol was applied to the total synthesis of (R)-phoracantholide I.

    2. STAT3 Inhibitors

      Ureido-Pyridazinone Derivatives: Insights into the Structural and Conformational Properties for STAT3 Inhibition

      Fiorella Meneghetti, Stefania Villa, Daniela Masciocchi, Daniela Barlocco, Lucio Toma, Dong-Cho Han, Byoung-Mog Kwon, Naohisa Ogo, Akira Asai, Laura Legnani and Arianna Gelain

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500599

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      The design, synthesis and biological properties of new potential STAT3 inhibitors with a pyridazinone ring, which replaces the 1,2,5-oxadiazole of previous investigated compounds, are described. A complete modeling study rationalized the results obtained and helped elucidate the structural and conformational properties needed for STAT3 inhibition.

    3. Solid Luminogens

      Identifying Solid Luminogens through Gold-Catalysed Intramolecular Hydroarylation of Alkynes

      Aslam C. Shaikh, S. Shalini, Ramanathan Vaidhyanathan, Manoj V. Mane, Ayan Kumar Barui, Chitta Ranjan Patra, Yeduru Venkatesh, Prakriti Ranjan Bangal and Nitin T. Patil

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500503

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      A gold-catalysed intramolecular hydroarylation approach for the synthesis of structurally novel pyrrolo-quinoxaline embedded coumarins is described. Their photophysical properties, as well as structural and theoretical investigations and application for live cell imaging, are discussed.

    4. Combinatorial Quinoline Synthesis

      Solid-Phase Friedländer Synthesis Using an Alkoxyamine Linker

      Kota Yamaguchi, Takeshi Noda, Toshiki Tomizawa, Eriko Kanai and Hideaki Hioki

      Article first published online: 30 JUN 2015 | DOI: 10.1002/ejoc.201500426

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      A quinoline library was prepared by combinatorial synthesis using an alkoxyamine linker. The oxime linkage formed by anchoring carbonyl compounds was highly robust under various reaction conditions. Desired quinolines were released by Friedländer reaction.

    5. Cyclic Imines

      Reactivity of N-Boc-Protected Amino-Ynones in the Presence of Zinc Chloride: Formation of Acetylenic Cyclic Imines and Their Palladium Complexes

      Huy-Dinh Vu, Jacques Renault, Thierry Roisnel, Clémence Robert, Philippe Jéhan, Nicolas Gouault and Philippe Uriac

      Article first published online: 29 JUN 2015 | DOI: 10.1002/ejoc.201500569

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      The reaction of γ- and δ-amino-ynones with ZnCl2 efficiently produced zinc complexes that were isolated as free acetylenic cyclic imines. Their ability to complex palladium was also investigated.

    6. Glyconanodiamonds

      Thiourea-Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion

      Claudia Fessele, Stefan Wachtler, Vijayanand Chandrasekaran, Carina Stiller, Thisbe K. Lindhorst and Anke Krueger

      Article first published online: 29 JUN 2015 | DOI: 10.1002/ejoc.201500532

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      Thiourea-bridging is a new approach to conjugating nanodiamond nanoparticles and biomolecules. This was exemplified by preparation of saccharide-functionalized nanodiamonds (NDs) that were characterized and employed in biological studies. These studies revealed specific ND binding to E. coli bacterial cells.

    7. Oxygen Heterocycles

      Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans

      Laura Antonella Aronica, Luca Giannotti, Giulia Tuci and Francesco Zinna

      Article first published online: 26 JUN 2015 | DOI: 10.1002/ejoc.201500539

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      A one-step synthesis of a set of functionalised dihydroisobenzofurans was accomplished through copper-free, palladium-catalysed cyclocarbonylative Sonogashira reactions between ethynylbenzyl alcohols and iodoarenes.

    8. Organophosphorus Chemistry

      Synthesis of a Phosphinate Analogue of the Antitumour Phospholipid Edelfosine

      Marios S. Markoulides and Andrew C. Regan

      Article first published online: 26 JUN 2015 | DOI: 10.1002/ejoc.201500477

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      A synthesis of a phosphinate analogue of the antitumour ether phospholipid edelfosine is described. Both phosphorus–oxygen bonds of the phosphate diester linkage in edelfosine are replaced by phosphorus–carbon bonds, in order to prevent hydrolytic cleavage. Free-radical addition and Michael-addition reactions are used to form the two phosphorus–carbon bonds.

    9. Diversity-Oriented Synthesis

      Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[b]benzofurans Based on Products from Anodic Oxidation of 2,4-Dimethylphenol

      Michael Mirion, Lars Andernach, Caroline Stobe, Joaquin Barjau, Dieter Schollmeyer, Till Opatz, Arne Lützen and Siegfried R. Waldvogel

      Article first published online: 25 JUN 2015 | DOI: 10.1002/ejoc.201500600

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      Starting from a simple phenol component an enantiomerically highly enriched pentacyclic spirolactone was obtained in three synthetic steps. The absolute configuration of the cyclopenta[b]benzofuran moiety with four countigous stereocenters was elucidated by combination of experimental and theoretical spectroscopy.

    10. Natural Product Chemistry

      Enantioselective Synthesis of Four Natural Homoisoflavonoids

      Yan-Chao Yu, Shijun Zhu, Xiao-Wei Lu, Yikang Wu and Bo Liu

      Article first published online: 25 JUN 2015 | DOI: 10.1002/ejoc.201500579

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      Four natural homoisoflavonoids were synthesized for the first time by using Evans' asymmetric aldol reaction to install the stereogenic center. The 1H and 13C NMR data of the synthetic samples were in agreement with the reported values, and the absolute configurations of three of the compounds were also established. Errors in previously reported NMR spectroscopic data/solvents were also revealed.

  7. Short Communications

    1. Metalated Cavitands

      Functionalized Metalated Cavitands via Imidation and Late-Stage Elaboration

      Yanchuan Zhao and Timothy M. Swager

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500714

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      Efficient methods to functionalize metalated cavitands are described. By using diversified iminophosphorane (PPh3=NR) reagents, π-conjugated pyrene, redox active ferrocene, and polymerizable norbornene moieties were successfully introduced. Furthermore, late-stage elaboration of the imido ligand provides facile access to complex architectures containing metalated cavitands.

    2. Synthetic Methods

      Synthesis of N-Acyl-N,O-acetals from Aldehydes, Amides and Alcohols

      Juliette Halli, Kamil Hofman, Tamara Beisel and Georg Manolikakes

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500655

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      A novel two-step protocol for the synthesis of N-acyl-N,O-acetals from amides, aldehydes and alcohols is reported. This method provides efficient and rapid access to synthetically useful N-acylimine precursors.

    3. Axial Chirality

      Synthesis of a C–N Axially Chiral N-Arylisatin through Asymmetric Intramolecular N-Arylation

      Atsuo Nakazaki, Keitaro Miyagawa, Noriaki Miyata and Toshio Nishikawa

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500593

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      The first synthesis of an enantiomerically pure C–N axially chiral N-arylisatin was accomplished from the corresponding N-aryloxindole, which was synthesized by an asymmetric intramolecular Buchwald–Hartwig N-arylation. This novel isatin would be a potentially versatile synthetic intermediate for a variety of 3,3-disubstituted oxindoles bearing a C3 stereogenic center.

    4. Silver(I) Catalysis

      Three-Component C1 Alkynylation of Tetrahydroisoquinolines Catalyzed by Silver Acetate

      Guang Shao, Yanjian He, Ying Xu, Jian Chen, Huijuan Yu and Rihui Cao

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500526

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      A highly efficient method to fulfil the three-component AgOAc-catalyzed C1 alkynylation of tetrahydroisoquinolines is developed. This reaction features excellent regioselectivity and mild reaction conditions, is oxidant free, and can be performed in air. This method is used to synthesize the core structure of tetrahydroberberine.

  8. Full Papers

    1. Functionalization of (Hetero)arenes

      CF3-Carbenoid C–H Functionalization of (Hetero)arenes under Chelation-Controlled RhIII Catalysis

      Irina E. Iagafarova, Daria V. Vorobyeva, Alexander S. Peregudov and Sergey N. Osipov

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500545

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      An efficient method for the CF3-carbenoid C–H functionalization of benzenes and indoles using readily available methyl 3,3,3-trifluoro-2-diazopropionate under chelation-controlled RhIII catalysis has been developed. The reaction proceeds with high regioselectivity and allows the simultaneous introduction of CF3 and COOMe groups into the 2-position of directing-group-containing benzenes and indoles.

    2. Protecting Groups

      4-(Acetylthio)-2,2-dimethyl-3-oxobutyl and 4-(tert-Butyldisulfanyl)-2,2-dimethyl-3-oxobutyl as Protecting Groups for Nucleoside 5′-Phosphoramidates Derived from L-Alanine Methyl Ester

      Vyankat A. Sontakke, Harri Lönnberg and Mikko Ora

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500531

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      4-(Acetylthio)-2,2-dimethyl-3-oxobutyl- and 4-(tert-butyldisulfanyl)-2,2-dimethyl-3-oxobutyl-protected nucleoside 5′-phosphoramidates are deprotected to give diester-like nucleoside 5′-phosphoramidate in the presence and absence of enzyme or glutathione at pH = 7.5 and 37.0 °C.

    3. Fused 1,2,3-Triazoles

      Tandem Organocatalyzed Knoevenagel Condensation/1,3-Dipolar Cycloaddition towards Highly Functionalized Fused 1,2,3-Triazoles

      Jubi John, Joice Thomas, Nikita Parekh and Wim Dehaen

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201500459

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      The synthesis of a wide range of 5–7 membered ring fused 1,2,3-triazoles has been realized through a tandem organocatalyzed reaction.

    4. Bicyclization

      One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of α,β-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate

      Lei Li, Jia-Jia Chen, Xing-Lan Kan, Lu Zhang, Yu-Long Zhao and Qun Liu

      Article first published online: 23 JUN 2015 | DOI: 10.1002/ejoc.201500414

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      A one-step synthesis has been developed for functionalized phenanthridinones by starting from readily available acyclic α,β-unsaturated carbonyl compounds that contain a 2-aminophenyl group at the β-position or carbonyl carbon and dimethyl glutaconate. The domino reaction proceeds through an intermolecular [3+3] annulation followed by an intramolecular aza-cyclization/aromatization process.

  9. Short Communications

    1. Shape Amphiphiles

      Self-Assembled Giant Vesicles Formed by Type I [3:3]-Hexakis Adducts of C60 Equipped with Enantiomerically Pure cyclo-Monomalonate Addends

      Charalambos P. Ioannou, Georgios I. Ioannou, Eleni E. Moushi, Kelly Velonia and Nikos Chronakis

      Article first published online: 23 JUN 2015 | DOI: 10.1002/ejoc.201500504

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      Two giant, amphiphilic type I [3:3]-hexakis adducts of C60 equipped with enantiomerically pure cyclo-monomalonate addends are prepared. Their self-assembling behavior in water reveals that minor modification of the size and chemical nature of their monomalonate addends and, consequently, of the shape of these giant molecules significantly influences their self-assembling architectures.

  10. Corrections

    1. You have free access to this content
      The Nugent–RajanBabu Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry

      Antonio Rosales, Ignacio Rodríguez-García, Juan Muñoz-Bascón, Esther Roldan-Molina, Natalia M. Padial, Laura Pozo Morales, Marta García-Ocaña and J. Enrique Oltra

      Article first published online: 23 JUN 2015 | DOI: 10.1002/ejoc.201500761

      This article corrects:
  11. Short Communications

    1. Peptide Catalysis

      Kinetic Resolution of a Planar-Chiral [2.2]Paracyclophane Derivative by Helical-Peptide-Catalyzed Michael Addition of Nitromethane

      Kengo Akagawa, Nobuhiro Nishi, Isao Yoshikawa and Kazuaki Kudo

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500594

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      A kinetic resolution of a planar-chiral [2.2]paracyclophane was attained through the Michael addition of nitromethane in the presence of a resin-supported peptide catalyst. A helical peptide with an appropriate N-terminal sequence was effective for a selective resolution.

  12. Full Papers

    1. Radical Alkylation

      Introduction of Ether Groups onto Electron-Deficient Nitrogen-Containing Heteroaromatics Using Radical Chemistry under Transition-Metal-Free Conditions

      Naoki Okugawa, Katsuhiko Moriyama and Hideo Togo

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500584

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      Electron-deficient nitrogen-containing heteroaromatics undergo thermal reaction with assorted ethers forming alkylated products in good to moderate yields under transition-metal-free conditions; their irradiation in the presence of benzoyl peroxide and crown ethers afforded corresponding lariat aza-crown ethers in good to moderate yields.

    2. Polycycles

      Synthesis of Polycycles by Single or Double Domino Nucleophilic Substitution/Diels–Alder Reaction

      Pelayo Camps, David Lozano and Mercè Font-Bardia

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500601

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      A short access to complex polycycles by domino nucleophilic substitution/Diels–Alder cycloaddition

  13. Microreviews

    1. Organometallic Rearrangements

      Formal Dyotropic Rearrangements in Organometallic Transformations

      Michael F. Croisant, Ryan Van Hoveln and Jennifer M. Schomaker

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500561

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      Organometallic dyotropic rearrangements involve interchange of two groups on a stationary scaffold by breaking and reforming of two σ bonds. They proceed through various different mechanisms and yield a diverse array of products. This microreview traces recent developments and applications of formal dyotropic rearrangements involving both stoichiometric and catalytic amounts of transition metals.

  14. Short Communications

    1. C–S Activation

      Palladium-Catalyzed Desulfurative Carbocyclizations of α-(3-Butenoyl) Ketene Dithioacetals in the Presence of Silanes

      Bangyu Liu, Jian Chang, Gang Zheng, Xiaoning Song and Mang Wang

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500453

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      A combination of palladium and silane has been well used for the catalytic desulfurative carbocyclization of α-(3-butenoyl) ketene dithioacetals leading to 2-cyclopentenones under neutral conditions. Thus, a new Heck-type cyclization based on C–S bond cleavage for the synthesis of spiro compounds by using silanes as the desulfurative agents has been established.

    2. Arsenical C-Glucoside Derivatives with Promising Antitumor Activity

      Giuseppe D'Orazio, Gelsomina Parisi, Claudia Policano, Rosella Mechelli, Giovanni Codacci Pisanelli, Michele Pitaro, Giovanni Ristori, Marco Salvetti, Francesco Nicotra and Barbara La Ferla

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500529

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      C-Glucoside derivatives covalently linked to the arsenic atom in different oxidation states have been synthesized. The C-glucoside conjugated to the phenyldithioarsolan group, showed promising antiproliferative activity on human neuroblastoma cells (SK-N-BE).

    3. Trifluoromethylthiolation

      Acid-Catalyzed Synthesis of α-Trifluoromethylthiolated Carbonyl Compounds

      Sébastien Alazet, Ermal Ismalaj, Quentin Glenadel, Didier Le Bars and Thierry Billard

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500710

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      One reagent, two possibilities: Complementary to previously described base-catalyzed reactions, α-trifluoromethylthiolations of carbonyl compounds were realized in soft acidic conditions with a second generation trifluoromethanesulfenamide. Different selectivities were then observed. With this new strategy, all types of CF3S-carbonyl compounds can be synthesized by starting from the same reagent.

  15. Full Papers

    1. Cascade Reaction

      Proline-Catalyzed Knoevenagel Condensation/[4+2] Cycloaddition Cascade Reaction: Application to Formal Synthesis of Averufin

      Haibo Tan, Xinzheng Chen, Huiyu Chen, Hongxin Liu and Shengxiang Qiu

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500559

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      A remarkable proline-catalyzed Knoevenagel condensation/[4+2] cycloaddition cascade reaction was uncovered for the construction of biologically interesting tricyclic ketal skeletons. This approach mimics a biosynthetic sequence and establishes a viable synthetic strategy for the efficient formal synthesis of averufin.

    2. Cycloadditions

      Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor–Acceptor Cyclobutanes and Nitrosoarenes

      Naresh Vemula and Brian L. Pagenkopf

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500542

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      The scope of Yb(OTf)3-catalyzed [4+2] cycloaddition between donor–acceptor (DA) cyclobutanes and nitrosoarenes is extended to additional DA cyclobutanes. Also, an unexpected formation of pyrrolidine products was discovered when 50 mol-% of MgI2 was used as a Lewis acid with electron-rich nitrosoarenes.

    3. Piperidine Synthesis

      Asymmetric Synthesis of δ-Chloro-β-amino-N-sulfinyl Imidates as Versatile Chiral Building Blocks for the Synthesis of 2,3-Disubstituted Piperidines

      Elena Semina, Filip Colpaert, Kristof Van Hecke, Norbert De Kimpe and Sven Mangelinckx

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500466

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      New δ-chloro-β-amino-N-sulfinyl-substituted imidates were synthesized by a highly anti-selective Mannich-type reaction, and were cyclized to give 2-aryl-N-sulfonylpiperidine-3-carbimidates in high yields. The latter were transformed into enantiomerically pure methyl 2-arylpiperidine-3-carboxylates and cis-3-amino-2-aryl-N-sulfonylpiperidines.

    4. C–N Bond Formation

      CuI-Mediated α-Ketoacylation of Sulfoximines under Solvent-Free Conditions

      Ya Zou, Zhihong Peng, Wanrong Dong and Delie An

      Article first published online: 22 JUN 2015 | DOI: 10.1002/ejoc.201500410

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      A new methodology for the construction of C–N bonds is herein reported. The reaction takes place under oxidative conditions, requires no base, ligands or solvents, and demonstrates excellent functional group compatibility. Moreover, control reactions suggest that the reaction proceeds through a dual C–H/N–H activation pathway.

    5. Synthetic Methods

      2,2′-Bis-substituted Biphenyls by the Addition of Nucleophiles to Benzyne Followed by In Situ Oxidative Homocoupling

      Friederike Sibbel, Constantin G. Daniliuc and Armido Studer

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500456

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      Three σ-bonds in one pot! Mg-anilides and -thiolates readily add to the reactive triple bond of benzyne to form an aryl-Grignard intermediate. In situ oxidative homocoupling of this species using CuII and dioxygen leads to 2,2′-bis-substituted biphenyls with interesting crystal structures

    6. Actinorhodins

      Synthetic Studies toward Actinorhodin and γ-Actinorhodin by using a Homo-coupling Strategy: Synthesis of Hemiactinorhodin and Hemi-γ-actinorhodin

      Sandip V. Mulay, Amit Bhowmik and Rodney A. Fernandes

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500510

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      A Dötz-type benzannulation/oxa-Pictet–Spengler-based synthesis of the pyranonaphthalene unit has been explored. The latter on oxidative dimerization failed to deliver the dimeric molecules, actinorhodin and -actinorhodin. However, the synthesis of hemiactinorhodin and hemi--actinorhodin was successfully achieved.

    7. Deoxyoligosaccharide Deprotection

      Reagent Control of a Birch Reduction for the Synthesis of a 2-Deoxyoligosaccharide Possessing a 1,4-Dialkylhydroquinone

      Sho Yamaguchi, Hiroshi Tanaka and Takashi Takahashi

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500515

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      We have developed a versatile deprotection method for the synthesis of 2-deoxyoligosaccharides containing a 1,4-dialkylhydroquinone moiety. Birch reduction with potassium and 1,3-pentadiene followed by treatment with mCPBA (m-chloroperoxybenzoic acid) provided a fully deprotected landomycin E deoxytrisaccharide in a satisfying yield.

    8. β-Amino Acids

      Scalable Enantioselective Synthesis of Fmoc-β2-Serine and Fmoc-β2-Threonine by an Organocatalytic Mannich Reaction

      Daniel Meyer, Roger Marti and Dieter Seebach

      Article first published online: 18 JUN 2015 | DOI: 10.1002/ejoc.201500636

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      The scalable diastereoselective Mannich reaction of functionalized aldehydes with phenethylamine-derived iminium precursors, by activation with prolines and prolinol derivatives is reported. The new robust process allows the simple preparation of enantiomerically pure Fmoc-protected β2-serine and β2-threonine on multi-gram quantities.

  16. Short Communications

    1. Oxidative Decarboxylative Coupling

      Silver-Catalyzed Aerobic Oxidative Decarboxylative Coupling of Arylpropiolic Acids with H-Phosphine Oxides: Mild and Facile Synthesis of β-Oxophosphine Oxides

      Yao-Fu Zeng, Dong-Hang Tan, Wen-Xin Lv, Qingjiang Li and Honggen Wang

      Article first published online: 16 JUN 2015 | DOI: 10.1002/ejoc.201500587

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      Aerobic oxidative decarboxylative coupling of arylpropiolic acids with H-phosphine oxides is realized under silver catalysis. The reaction proceeds smoothly under mild conditions to give β-oxophosphine oxides in moderate to good yields. Preliminary mechanistic studies are conducted.

  17. Full Papers

    1. Pyrazole Synthesis

      Regioselective, One-Pot, Three-Component Synthesis of 1,3,4- and 1,3,5-Triarylpyrazoles from 1- and 2-Aryl-1-alkenyl Sulfones

      Shinichiro Fuse, Hirotaka Sugiyama, Daisuke Kobayashi, Yusuke Iijima, Keisuke Matsumura, Hiroshi Tanaka and Takashi Takahashi

      Article first published online: 16 JUN 2015 | DOI: 10.1002/ejoc.201500562

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      One-pot, three-component couplings of aldehydes with hydrazines and arylalkenyl sulfones for the regioselective syntheses of 1,3,4- and 1,3,5-triarylpyrazoles were demonstrated. In our developed procedure, DDQ worked as an effective oxidant, and the addition of a strong acid was not required. This allowed the synthesis of various pyrazoles in good yields.

    2. C–H Functionalization

      Chemoselective Pd-Catalyzed Isocyanide Insertion Reaction of Enaminones by C–H Functionalization: Hydrolysis or Cyclization through 1,3-Palladium Migration

      Zheng-Yang Gu, Xiang Wang, Jia-Jia Cao, Shun-Yi Wang and Shun-Jun Ji

      Article first published online: 16 JUN 2015 | DOI: 10.1002/ejoc.201500458

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      A chemoselective palladium-catalyzed isocyanide insertion reaction of enaminones was developed. Amide derivatives were synthesized by this C–H functionalization and subsequent hydrolysis reactions, and 4-aminoquinoline derivatives were prepared by this C–H functionalization, which includes a 1,3-palladium migration in the process.

    3. Water and pH Sensor

      A Tris(hydroxymethyl)aminomethane-Rhodamine Spirolactam Derivative as Dual Channel pH and Water Sensor and Its Application to Bio Imaging

      Manisha Devi, Abhimanew Dhir and Chullikkattil P. Pradeep

      Article first published online: 16 JUN 2015 | DOI: 10.1002/ejoc.201500415

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      A rhodamine spirolactam derivative, R1 has been synthesized and characterized. R1 shows visual colour change and strong fluorescence in trace amount of water in organic solvents and also over a wide pH range (pH 3–9). R1 is applicable in cell imaging of nucleus of Allium cepa root tip cells and human WBCs.

    4. Olefination Selectivity

      RhIII-Catalyzed Olefination of 2-Aryloxy­pyridines Using 2-Pyridyloxyl as the Removable Directing Group

      Arun Jyoti Borah, Guobing Yan and Lianggui Wang

      Article first published online: 15 JUN 2015 | DOI: 10.1002/ejoc.201500530

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      A cationic RhIII-catalyst has been found to be very effective for trans selective ortho-olefination of 2-aryloxypyridines using a removable 2-pyridyloxyl directing group compatible with a wide scope of olefinic coupling partners. The trans-stilbene derivatives are generated in high yields under solvent free conditions and, upon directing group removal, phenol derivatives are unveiled.

    5. Sonogashira Cross-Coupling

      Scope and Mechanistic Limitations of a Sonogashira Coupling Reaction on an ­Imidazole Backbone

      Alexander H. Sandtorv and Hans-René Bjørsvik

      Article first published online: 15 JUN 2015 | DOI: 10.1002/ejoc.201500520

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      A Sonogashira coupling reaction to functionalize an imidazole backbone was developed and investigated. Coupling success was predicted by molecular electrostatic potential surfaces (MEPS) for the reagents there were within a narrow range (–94 to –105 kJ mol–1). Auxiliary groups favorably influenced MEPS and enabled coupling, which verifies that our model is in agreement with experimental results.

    6. Extended π-Systems

      Syntheses, Structures and Conformational Dynamics of 1,3,5-Tris(3″-ethynylbi­phen­yl-2′-yl)benzene Derivatives

      Daniel Trawny, Marcel Quennet, Nadine Rades, Dieter Lentz, Beate Paulus and Hans-Ulrich Reissig

      Article first published online: 15 JUN 2015 | DOI: 10.1002/ejoc.201500615

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      The conformational dynamic of a novel chloro-substituted 1,3,5-tris(3″-iodobiphenyl-2′-yl)benzene was investigated by temperature-dependent 1H NMR spectroscopy and DFT calculations. The crystal structures of the chloro-substituted derivative and its non-halogenated analog reveal different solid-state conformations. During the preparation of these trialkynes, iodine monochloride was successfully applied as tandem-desilylation-chlorination reagent. Finally bipyridine end groups were installed at the trialkyne leading to a unique trivalent bipyridine derivative.

  18. Short Communications

    1. Synthesis and Reactivity of N-tert-Butanesulfinyl Glycosylamines

      Chloé Cocaud, Cyril Nicolas, Alexandre Bayle, Thomas Poisson, Xavier Pannecoucke and Olivier R. Martin

      Article first published online: 15 JUN 2015 | DOI: 10.1002/ejoc.201500487

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      The synthesis and reactivity of N-tert-butanesulfinyl glycosylamines with Grignard reagents was investigated for the first time. These scaffolds provide more reliable and versatile synthetic intermediates en route to important compounds such as iminosugar-C-glycosides than the corresponding N-alkyl- and N-Cbz-N-glycosylamines.

  19. Full Papers

    1. Thioacetate Synthesis

      Bismuth(III)-Promoted Acetylation of Thio­ethers into Thioacetates

      Martyn Jevric, Anne Ugleholdt Petersen, Mads Mansø, Anders Østergaard Madsen and Mogens Brøndsted Nielsen

      Article first published online: 15 JUN 2015 | DOI: 10.1002/ejoc.201500420

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      Conversion of tert-butyl thioethers into thioacetates is conveniently performed by the action of acetyl chloride and bismuth(III) triflate. The thioacetate group is extensively employed as electrode anchoring group in molecular electronics, and we show that these gentle conditions allow the preparation of a large selection of target molecules of interest as molecular wires.

    2. Sulfur Heterocycles

      Synthesis of endo- and exo-N-Protected 5-Arylated 2-Aminothiazoles through Direct Arylation: An Efficient Route to Cell Differentiation Accelerators

      Toan Dao-Huy, Birgit J. Waldner, Laurin Wimmer, Michael Schnürch and Marko D. Mihovilovic

      Article first published online: 12 JUN 2015 | DOI: 10.1002/ejoc.201500283

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      An improved protocol for the direct arylation of N-phenyl-N-benzyl(thiazol-2-yl)amines and regioisomeric 3-benzyl-N-phenylthiazol-2(3H)-imine is described. The two substrates for the arylation were obtained from a common starting material. In the latter case, the regioselectivity of arylation occurs exclusively in the 5-position.

  20. Microreviews

    1. Hydrogen-Transfer Reactions

      Pd-Catalyzed Hydrogen-Transfer Reactions from Alcohols to C=C, C=O, and C=N Bonds

      Jacques Muzart

      Article first published online: 12 JUN 2015 | DOI: 10.1002/ejoc.201500401

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      Highlights and mechanisms of Pd-catalyzed abstracting and borrowing hydrogen transfers from alcohols are presented.

  21. Full Papers

    1. Privileged Scaffolds

      A One-Pot Synthesis of Triazolodiazepines

      Geert Hooyberghs, Sofie Van Hove, Jeroen Jacobs, Luc Van Meervelt and Erik V. Van der Eycken

      Article first published online: 12 JUN 2015 | DOI: 10.1002/ejoc.201500402

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      A one-pot two-step approach to novel [1,2,3]triazolo[1,5-a]diazepines has been developed. A variety of triazolodiazepines with possible biological activity is presented.

    2. Reaction Mechanisms

      A Theoretical Probe of Mechanistic Trichotomy in RhIII-Catalyzed Annulation with Alkyne MIDA Boronates: Roles of Salt, Solvent, and Coupling Partner

      Liu Zhao and De-Cai Fang

      Article first published online: 12 JUN 2015 | DOI: 10.1002/ejoc.201500329

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      The reaction mechanisms, the role of salts, solvent effects, and substrate scope in the RhIII-catalyzed C–H activation and annulation of N-(pivaloyloxy)benzamide and alkyne MIDA boronates have been investigated by DFT calculations.

    3. Alkyl Aryl Ethers

      Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides

      Ying Guo, Xue-Min Fan, Min Nie, Hong-Wei Liu, Dao-Hua Liao, Xian-Dao Pan and Ya-Fei Ji

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500500

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      An efficient and practical ligand-free CuBr-catalysed short-chain alkoxylation of unactivated aryl bromides is described. A sodium alkoxide nucleophile is used in the alcohol as solvent. The corresponding alkyl formate is used as a noncontaminating cocatalyst, and inorganic lithium chloride as an additive.

    4. Catalytic Olefinations

      Scope and Limitation of the Microwave-Assisted Catalytic Wittig Reaction

      Marcel Hoffmann, Sunetra Deshmukh and Thomas Werner

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500310

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      The scope and limitations of the microwave-assisted catalytic Wittig reaction have been evaluated with respect to the catalyst, silane, solvent, reaction conditions, and substrates.

    5. Cycloaddition Reactions

      Synthesis of Chromen[4,3-b]pyrrolidines by Intramolecular 1,3-Dipolar Cycloadditions of Azomethine Ylides: An Experimental and Computational Assessment of the Origin of Stereocontrol

      Paulo R. R. Costa, José M. Sansano, Unai Cossío, Julio C. F. Barcellos, Ayres G. Dias, Carmen Nájera, Ana Arrieta, Abel de Cózar and Fernando P. Cossío

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500434

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      The two-component synthesis of chromene[4,3-b]pyrrolidines has been achieved under two different conditions. The strategy was used to obtain N-sulfonylated adducts with interesting biological activity. Calculations show that formation of W and S′ 1,3-dipoles determines the stereochemical outcome of the reaction, which involves asynchronous transition structures.

    6. Sequential Annulation

      Nucleophilic-Bisphosphine-Catalysed One-Pot Sequential [4+2]/[4+2] Annulation of an Allenoate with Benzylidenepyrazolones

      Yu Jia, Xiao Tang, Guowei Cai, Ruxuan Jia, Boran Wang and Zhiwei Miao

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500399

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      Spiro-pyrazolidinones have been synthesized through a bisphosphine-triggered sequential [4+2]/[4+2] annulation reaction of 4-benzylidene-5-methyl-2-phenyl-2,4-dihydropyrazolone with a γ-benzyl-substituted allenoate in moderate yields.

    7. Natural Products

      Eringiacetal A, 5,6-seco-(5S,6R,7R,9S)-5,6:5,7:6,9-Triepoxyergosta-8(14),22-diene-3β,7β-diol, an Unusual Ergostane Sterol from the Fruiting Bodies of Pleurotus eryngii

      Takashi Kikuchi, Yuki Masumoto, Yasuko In, Koji Tomoo, Takeshi Yamada and Reiko Tanaka

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500382

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      A new rearranged ergostane-type steroid, named eringiacetal A, was isolated from the fruiting bodies of Pleurotus eryngii (Pleurotaceae). Its structure was established by spectroscopic analyses and X-ray crystallography. Eringiacetal A features an unprecedented 5,6-seco-(5S,6R,7R,9S)-5,6:5,7:6,9-triepoxyergosta-8(14),22-diene-3β,7β-diol.

    8. Xanthone Dyads

      (E)-2-(4-Arylbut-1-en-3-yn-1-yl)chromones as Synthons for the Synthesis of Xanthone-1,2,3-triazole Dyads

      Hélio M. T. Albuquerque, Clementina M. M. Santos, José A. S. Cavaleiro and Artur M. S. Silva

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500448

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      Two different strategies are described for the synthesis of a series of new xanthone-1,2,3-triazole dyads. This objective is achieved using novel (E)-2-(4-arylbut-1-en-3-yn-1-yl)chromones as building blocks amenable to critical cycloaddition reactions.

    9. Cross-Coupling

      Synthesis of 2-X-, 3-X-4,4′-Dicyanobiphenyls (X = CH3, OCH3, F) by Cross-Coupling of the Terephthalonitrile Dianion with Substituted Benzonitriles

      Roman Yu. Peshkov, Elena V. Panteleeva, Lyudmila N. Shchegoleva, Irina Yu. Bagryanskaya, Tatyana V. Rybalova, Nadezhda V. Vasilieva and Vitalij D. Shteingarts

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500295

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      Transition-metal-free biaryl cross-coupling utilises the terephthalonitrile dianion sodium salt for para-cyanophenylation of aromatic nitriles modified with methoxy, methyl, and fluorine substituents, with the formation of 2- and 3-substituted 4,4′-dicyanobiphenyls. The proposed reaction scheme is verified by quantum chemical calculations.

    10. NHCs in Synthesis

      Organic Synthesis with N-Heterocyclic Carbenes of Indazole: Synthesis of Benzo(thio)imidates, Benzo[d][1,3]thiazines and Quinazoline-4-thiones

      Zong Guan, Martin Nieger and Andreas Schmidt

      Article first published online: 10 JUN 2015 | DOI: 10.1002/ejoc.201500331

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      N-Heterocyclic carbenes of indazoles are suitable starting materials for the synthesis of new 2-anilinobenzothioimidates (12 examples). The heterocyclic ring systems of benzo[d][1,3]thiazines and quinazoline-4-thiones are available via benzamides, formed from indazol-3-ylidene, which cyclize with aldehydes (12 examples).

    11. Isocyanide Chemistry

      Modular Access to Tetrasubstituted Imidazolium Salts through Acid-Catalyzed Addition of Isocyanides to Propargylamines

      Ouldouz Ghashghaei, Marc Revés, Nicola Kielland and Rodolfo Lavilla

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500502

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      Propargylamines, synthesized through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. Tandem one-pot protocols allow direct access to these adducts from the commercially available inputs.

    12. Propeller-Shaped Macrocycles

      Propeller-Shaped D3h-Symmetric Macrocycles with Three 1,8-Diazaanthracene Blades as Building Blocks for Photochemically Induced Growth Reactions

      Marco Servalli, Luzia Gyr, Junji Sakamoto and A. Dieter Schlüter

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500496

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      A new class of propeller-shaped macrocycles is accessible via a six-step procedure with overall yields ranging from 6–16 %. These cyclophanes are equipped with 1,8-diazaanthracene units and are designed for photochemical growth reactions in two dimensions.

    13. C–C Bond Cleavage

      Copper-Catalyzed Intramolecular C–C Bond Cleavage To Construct 2-Substituted Quinazolinones

      Ben-Quan Hu, Li-Xia Wang, Luo Yang, Jun-Feng Xiang and Ya-Lin Tang

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500473

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      The C–C bond at the 2-position of 2,2-disubstituted-1,2,3,4-tetrahydroquinazolinones was selectively cleaved by a Cu/air catalytic system to construct 2-substituted quinazolinones. The trend for the cleavage of the C–C bond was dependent on the leaving group in the order of: alkyl > methyl > phenyl > substituted aryl.

    14. [6π+2π]-Cycloaddition

      Titanium-Catalyzed [6π+2π]-Cycloaddition of Alkynes and Allenes to 7-Substituted 1,3,5-Cycloheptatrienes

      Vladimir A. D'yakonov, Gulnara N. Kadikova, Dmitry I. Kolokol'tsev, Ilfir R. Ramazanov and Usein M. Dzhemilev

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500442

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      Titanium-catalyzed [6π+2π]-cycloaddition of 1,2-dienes and alkynes to 7-substituted 1,3,5-cycloheptatrienes, gives substituted bicyclo[4.2.1]nona-2,4-dienes and bicyclo[4.2.1]nona-2,4,7-trienes in high yields. The reaction mechanism was studied through quantum chemical modeling of the cycloheptatriene and acetylene interaction with the TiCl4–Et2AlCl system at the B3LYP/6-31G(d) level.

    15. Glycosidase Inhibitors

      ortho-Carborane-Modified N-Substituted Deoxynojirimycins

      Sascha Hoogendoorn, Elliot D. Mock, Anneke Strijland, Wilma E. Donker-Koopman, Hans van den Elst, Richard J. B. H. N. van den Berg, Johannes M. F. G. Aerts, Gijsbert A. van der Marel and Herman S. Overkleeft

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500364

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      The synthesis of a series of ortho-carborane-containing deoxynojirimycin (DNM) derivatives is described. The resulting compounds are potent inhibitors of human glucosylceramidases and glucosylceramide synthase, with inhibitory profiles comparable to those of the corresponding adamantyl-DNM derivatives.

    16. C–H Bond Activation

      Pd-Catalysed Direct Arylation of Heteroaromatics Using (Poly)halobenzene­sulfonyl Chlorides as Coupling Partners: One Step Access to (Poly)halo-Substituted Bi(hetero)aryls

      Aymen Skhiri, Anissa Beladhria, Kedong Yuan, Jean-Francois Soulé, Ridha Ben Salem and Henri Doucet

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500354

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      Pd-catalysed desulfitative arylation using 2-, 3- or 4-halo-substituted benzenesulfonyl chlorides affords arylated heteroarenes in moderate to high yields without cleavage of the C–halogen bonds, thereby enabling further transformations. Even 4-iodobenzenesulfonyl chloride, di- and tri-bromobenzenesulfonyl chlorides were successfully coupled.

  22. Corrections

    1. You have free access to this content
      Organocatalytic Asymmetric Fluorination of 4-Substituted Isoxazolinones

      Huanrui Zhang, Baomin Wang, Longchen Cui, Xiaoze Bao, Jingping Qu and Yuming Song

      Article first published online: 9 JUN 2015 | DOI: 10.1002/ejoc.201500650

      This article corrects:
  23. Full Papers

    1. Asymmetric Dearomatization

      Asymmetric Dearomatization of 1-Amino­naphthalene Derivatives through C–C Bond Formation with Electron-Rich Heterocycles as Nucleophiles

      Takafumi Baba, Junko Oka, Keiichi Noguchi and Ken Tanaka

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500486

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      A cationic gold(I)/axially chiral biaryl bis(phosphine) complex has been employed to catalyze the asymmetric dearomatization of 1-aminonaphthalene derivatives through a C–C bond-forming reaction with electron-rich heterocycles as the nucleophiles. These reactions afford pentacyclic heterocycles in good yields with moderate enantiomeric excess (ee) values.

    2. Small Molecules

      Low-Energy-Gap Organic Based Acceptor–­Donor–Acceptor π-Conjugated Small Molecules for Bulk-Heterojunction Organic Solar Cells

      Edison Castro, Andrea Cabrera-Espinoza, Eva Deemer and Luis Echegoyen

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500552

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      We synthetized two new electron-donor molecules based on an acceptor–donor–acceptor (A–D–A) structure. The optoelectronic, morphological and photovoltaic properties were studied. Optimized photovoltaic device fabrication based on ECTBT and [6,6]-phenyl-C70-butyric acid methyl ester (PC71BM) in a 1:1.5 ratio (w/w) exhibited the best energy conversion efficiency (PCE), at 3.26 %.

  24. Short Communications

    1. Energetic Materials

      Synthesis and Energetic Properties of 4-Diazo-2,6-dinitrophenol and 6-Diazo-3-hydroxy-2,4-dinitrophenol

      Thomas M. Klapötke, Andreas Preimesser and Jörg Stierstorfer

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500465

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      The very sensitive diazophenol derivatives diazo-2,6-dinitrophenol and 6-diazo-3-hydroxy-2,4-dinitrophenol could be synthesized by nitration reactions. They are promising alternatives to the commercially used sensitizer DDNP (2-diazo-4,6-dinitrophenol).

    2. Asymmetric Aldol Reaction

      Asymmetric Aldol Reaction of α,α-Disubstituted Acetaldehydes Catalyzed by Diphenylprolinol Silyl Ether for the Construction of Quaternary Stereogenic Centers

      Yujiro Hayashi, Hiroki Shomura, Qianqian Xu, Martin J. Lear and Itaru Sato

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500585

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      Diphenylprolinol silyl ether is an effective organocatalyst in the asymmetric cross-aldol reaction of α,α-disubstituted acetaldehydes with commercial ethyl glyoxylate polymer to generate all-carbon quaternary stereogenic centers with good enantioselectivity.

    3. Oxidative Heck Reaction

      Oxidative Heck Reaction of Fluorinated Olefins with Arylboronic Acids by Palladium Catalysis

      Yang Li, Dong-Huai Tu, Yu-Jie Gu, Bo Wang, Yao-Yu Wang, Zhao-Tie Liu, Zhong-Wen Liu and Jian Lu

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500597

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      The first examples of the palladium-catalyzed oxidative Heck reaction of 2,3,3,3-tetrafluoroprop-1-ene with various arylboronic acids is presented. This method provides a direct route to access (Z)-β-fluoro-β-(trifluoromethyl)styrenes with high stereoselectivity.

    4. Cycloaddition

      Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitro­alkene Catalyzed by Diphenylprolinol Silyl Ether

      Shigenobu Umemiya and Yujiro Hayashi

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500623

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      cis-Disubstituted nitropentenes are obtained with excellent diastereoselectivities and enantioselectivities by a formal [3+2] cycloaddition reaction. The first reaction is a domino reaction composed of the diphenylprolinol silyl ether mediated Michael reaction of nitroalkene with succinaldehyde followed by a Henry reaction. The next reaction is a dehydration achieved by using Ac2O and pyridine.

  25. Full Papers

    1. Asymmetric Organocatalysis

      Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure

      Ryo Horinouchi, Kouhei Kamei, Riki Watanabe, Nobushige Hieda, Naoki Tatsumi, Keiji Nakano, Yoshiyasu Ichikawa and Hiyoshizo Kotsuki

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500411

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      The Michael addition reaction of α-substituted cyclic ketones was efficiently promoted by a primary amine-based organocatalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran.

    2. Selenium Chemistry

      Cyclization of Diaryl(hetaryl)alkynes under Selenobromination Conditions: Regioselectivity and Mechanistic Studies

      Edgars Paegle, Sergey Belyakov, Marina Petrova, Edvards Liepinsh and Pavel Arsenyan

      Article first published online: 5 JUN 2015 | DOI: 10.1002/ejoc.201500431

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      The cyclization of substituted diaryl(hetaryl)alkynes with in-situ-prepared SeBr4 has been achieved. The use of an alkene additive as a bromine scavenger gives simple access to functionalized benzo[b]selenophene and selenophenothiophene derivatives from commercially available or easily accessible starting materials.

  26. Short Communications

    1. Nitrogen Heterocycles

      Practical Synthesis of Polysubstituted Haloimidazoles from 1,1-Dibromoalkenes and Amidines

      Yibiao Li, Liang Cheng, Yan Shao, Shaohua Jiang, Jialing Cai and Ning Qing

      Article first published online: 3 JUN 2015 | DOI: 10.1002/ejoc.201500305

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      The copper-catalyzed cycloamination reaction of 1,1-dibromoalkenes with amidines affords a diverse set of polysubstituted haloimidazole derivatives. Moderate to good yields with high regio- and chemoselectivities were achieved by using 4,7-diphenyl-1,10-phenanthroline as ligand without the addition of expensive catalyst.

    2. Diels–Alder Reactions

      Hydrazones as Productive Dienophiles in the Inverse Electron Demand Diels–Alder Reactions of 1,3,5-Triazines

      Kai Yang, Zhen Yang, Qun Dang and Xu Bai

      Article first published online: 3 JUN 2015 | DOI: 10.1002/ejoc.201500499

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      Through investigation of substituent effects and optimization of reaction conditions, oximes and hydrazones are introduced as productive dienophiles to expand the scope of the inverse electron demand Diels–Alder (IEDDA) reactions of 1,3,5-triazines, leading to the desired IEDDA products in moderate (for oximes) to excellent (for hydrazones) yields.

  27. Full Papers

    1. Macrolide Synthesis

      [3]-1-Azadendralenes as Versatile Building Blocks for the Stereoselective Synthesis of Polysubstituted Hexahydroquinazolin-2-ones and Hexahydrobenzothiazine-2-­imines

      Satoru Kobayashi, Kenji Kudo, Ai Ito, Takuya Honjo, Masahiro Yata, Takashi Otani, Noriki Kutsumura, Takao Saito, Fabienne Berrée, Elise Romain, Fabien Tripoteau and Bertrand Carboni

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500474

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      The diene-transmissive hetero Diels–Alder reaction of cross-conjugated 1-azatrienes was developed to produce stereoselectively ring-fused nitrogen heterocycles. [4+2] cycloaddition reaction with tosyl isocyanate or aryl isothiocyanates gave regioselectively monocycloadducts that reacted with dienophiles. Skeletal diversity is achieved by the addition sequence of the three reaction partners.

    2. Synthetic Methods

      Rhodium-Catalyzed Hydrosilylation Reaction of N-Sulfonyl-1,2,3-triazoles with Triphenylsilane: Access to Diverse Compounds

      Hui Wang, Hongwei Qiao, Hao Zhang, Haijun Yang, Yufen Zhao and Hua Fu

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500455

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      A highly efficient rhodium-catalyzed hydrosilylation reaction of N-sulfonyl-1,2,3-triazoles has been developed, and (E)-2-(triphenylsilyl)-2-aryl-N-(arylsulfonyl)ethenamines and 2-(triphenylsilyl)-2-aryl-N-(arylsulfonyl)ethanamines were obtained in good to excellent yields.

    3. Catalytic Enantioselective Synthesis of α-(Benzylamino)cyclobutanones

      Nicola Melis, Lorenza Ghisu, Régis Guillot, Pierluigi Caboni, Francesco Secci, David J. Aitken and Angelo Frongia

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500460

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      An organocatalytic enantioselective synthesis of α-(benzylamino)cyclobutanones has been achieved by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction. The reaction sequence began from readily available racemic α-hydroxycyclobutanone and a variety of benzylamines to afford the products in good to high yields and with moderate to high stereoselectivities.

    4. Metathesis Reactions

      1,1′-Dialkynylferrocenes as Substrates for Bidirectional Alkyne Metathesis Reaction

      Jingxiang Ma, Nico Krauße and Holger Butenschön

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500483

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      Bidirectional alkyne metathesis has been investigated as an alternative method to the usual palladium-coupling strategies for the construction of ferrocene-based molecular wires.

    5. Switchable Heterocyclizations

      Study of the Chemoselectivity of Multi­component Heterocyclizations Involving 3-Amino-1,2,4-triazole and Pyruvic Acids as Key Reagents, and Biological Activity of the Reaction Products

      Maryna V. Murlykina, Yana I. Sakhno, Sergey M. Desenko, Svetlana V. Shishkina, Oleg V. Shishkin, Dmytro O. Sysoiev, Maryna N. Kornet, Dominique Schols, Jan L. Goeman, Johan Van der Eycken, Erik V. Van der Eycken and Valentin A. Chebanov

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500469

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      The chemoselectivity of switchable three-component heterocyclizations involving 3-amino-1,2,4-triazole, aldehydes, and pyruvic acids were studied. The antimicrobial and antiviral activity of the products was screened.

    6. Macrolide Synthesis

      The Synthesis of Desepoxy-Isotedanolide – A Potential Biosynthetic Precursor of Tedanolide

      Arun Naini, Jörg Fohrer and Markus Kalesse

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500568

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      The putative precursor of tedanolide, desepoxy-isotedanolide, was synthesized based on a modified protecting group strategy. In contrast to tedanolide, the expected secondary hydroxyl group is incorporated into the lactone group. This potential precursor serves as a tool to gain information about the hypothetical evolutionary optimization of natural products' biological profile.

    7. Bicyclic Compounds

      Concise Construction of Bicyclo[6.4.0] and -[7.4.0] Frameworks by [4+2] Cycloaddition of 3,4-Dimethylene-2,5-bis(phenylsulfonyl)cycloalk-1-enes

      Chisato Mukai, Masanobu Ueda, Yasuhito Takahashi and Fuyuhiko Inagaki

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500598

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      An efficient procedure for the preparation of bicyclo[m.4.0] frameworks (m = 6, 7) from 3,4-dimethylenecycloalkenes by Diels–Alder or hetero-Diels–Alder [4+2] cycloadditions with dienophiles is developed. The resulting oxabicyclo[7.4.0] derivatives can be converted into δ-lactones. Thus, this method enables us to construct the core bicyclic frameworks of natural products (e.g., blumiolide C).

  28. Microreviews

    1. Unique Lewis Acid Catalysis

      Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis

      Haruro Ishitani, Hirotsugu Suzuki, Yuki Saito, Yasuhiro Yamashita and Shū Kobayashi

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500423

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      This microreview summarizes examples of Hf(OTf)4-mediated or -catalyzed organic reactions. Hafnium triflate shows outstanding performance in catalytic Friedel–Crafts acylation reactions and in Mannich-type reactions of imines, hydrazones, and N,O-acetals.

  29. Full Papers

    1. Substituted Carbazoles

      Access to Substituted Carbazoles in Water by a One-Pot Sequential Reaction of α,β-Substituted Nitro Olefins with 2-(3-Formyl-1H-indol-2-yl)acetates

      Soumen Biswas, Anuradha Dagar, Anvita Srivastava and Sampak Samanta

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500470

      Thumbnail image of graphical abstract

      A one-pot sequential reaction between α,β-disubstituted nitro olefins or α,δ-disubstituted nitro-dienes and 2-(3-formyl-1H-indol-2-yl)acetates was carried out followed by an in situ aromatization to afford polyfunctionalized carbazole derivatives in good to excellent yields. This π-extension method tolerates several functional groups and is performed under mild conditions. (DABCO = 1,4-diazabicyclo[2.2.2]octane)

    2. Mutarotation

      An Unexpected Pathway to Enantiomerization of Hemithioketals in Toluene Involving a Dimeric Transition State: A Combined Experimental and Computational Study

      Andrea Bottoni, Matteo Calvaresi, Barbara Cosimelli, Andrea Mazzanti, Mirella Rambaldi and Domenico Spinelli

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500421

      Thumbnail image of graphical abstract

      NMR and DFT calculations showed how a spontaneous enantiomerization of hemithioketals occurring in toluene involves a dimeric transition state.

    3. Silver Catalysis

      Silver Triflate Catalyzed Cyclopropyl ­Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis

      Philip Wai Hong Chan, Wan Teng Teo, Shaun Wei Yong Koh, Bo Ra Lee, Benjamin James Ayers, Dik-Lung Ma and Chung-Hang Leung

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500374

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      An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement to prepare benzo[b]oxepines and 2H-chromenes has been developed by starting from [cyclopropyl(hydroxy)methyl]phenols. A catalytic synergy was observed between the silver(I) cation and the triflate anion, which furnished the functionalized oxygen heterocycles.

    4. Natural Product Chemistry

      Conversion of Dihydroartemisinic Acid into Dihydro-epi-deoxyarteannuin B

      Hui-Jun Chen, Hong-Dong Hao and Yikang Wu

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500291

      Thumbnail image of graphical abstract

      The conversion of dihydroartemisinic acid into dihydro-epi-deoxyarteannuin B, a difficult transformation that defied exhaustive efforts in a previous study, can now be readily achieved in excellent yields with Pd(OAc)2/CuCl2/MnO2. This finding makes it easier to access a range of other arteannuins and several potent trioxane-type antimalarial agents.

  30. Microreviews

    1. Heterocycle Synthesis

      The Aza-Achmatowicz Reaction: Facile Entry into Functionalized Piperidinones

      Ferdi van der Pijl, Floris L. van Delft and Floris P. J. T. Rutjes

      Article first published online: 28 MAY 2015 | DOI: 10.1002/ejoc.201500321

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      The aza-Achmatowicz reaction encompasses the oxidative rearrangement of readily accessible α-furanylamines into the corresponding piperidinones. The latter building blocks are synthetically versatile scaffolds that have been extensively used for the synthesis of bioactive compounds and natural products, rendering the aza-Achmatowicz reaction an important synthetic transformation.

    2. Organocatalysis

      Trifunctional Organocatalysts: Catalytic Proficiency by Cooperative Activation

      Ryan Kenny and Fei Liu

      Article first published online: 28 MAY 2015 | DOI: 10.1002/ejoc.201500179

      Thumbnail image of graphical abstract

      Proficient trifunctional organocatalysts employ an expansive collection of chemical motifs in multiple modes of activation to provide concurrent enhancement in rate and enantioselectivity in complex reactions. These systems demonstrate catalytic cooperativity for a range of C–C, C–N, C–O, and C–X bond-forming reactions.

  31. Full Papers

    1. Insect Pheromone Research

      Pheromone Bouquet of the Dried Bean Beetle, Acanthoscelides obtectus (Col.: Chrysomelidae), Now Complete

      József Vuts, Wittko Francke, Kenji Mori, Paulo H. G. Zarbin, Antony M. Hooper, Jocelyn G. Millar, John A. Pickett, Miklós Tóth, Keith Chamberlain, John C. Caulfield, Christine M. Woodcock, Armin G. Tröger, Éva Bálintné Csonka and Michael A. Birkett

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500196

      Thumbnail image of graphical abstract

      The male-produced sex pheromone of the dried bean beetle Acanthoscelides obtectus consists of ethyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z)-decadienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, octadecanal and (3Z,6E)- as well as (3E,6E)-α-farnesene. A complete blend of synthetic compounds in natural proportions was as attractive as the natural signal.

  32. Microreviews

    1. The Nugent Reagent

      The Nugent Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry

      Antonio Rosales, Ignacio Rodríguez-García, Juan Muñoz-Bascón, Esther Roldan-Molina, Natalia M. Padial, Laura Pozo Morales, Marta García-Ocaña and J. Enrique Oltra

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500292

      Thumbnail image of graphical abstract

      The different reactions promoted and/or catalysed by the Nugent reagent, a contemporary single-electron transfer agent, are reported. The combination of radical intermediates and transition-metal catalysis is an excellent tool for the development of new and efficient synthetic procedures.

      Corrected by:

      Correction: The Nugent–RajanBabu Reagent: A Formidable Tool in Contemporary Radical and Organometallic Chemistry

      Article first published online: 23 JUN 2015

    2. β-Fluorinated Amines

      Advancements in Aminofluorination of ­Alkenes and Alkynes: Convenient Access to β-Fluoroamines

      Pinhong Chen and Guosheng Liu

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500231

      Thumbnail image of graphical abstract

      Direct aminofluorination of alkenes enables the convenient synthesis of β-fluorinated amine compounds, which are important and valuable building blocks in medicinal chemistry. This review covers recently developed methods for aminofluorination of alkenes, mainly focusing on transition-metal-catalyzed pathways.

    3. Niobium Complex Chemistry

      Niobium Complexes in Organic Transformations: From Stoichiometric Reactions to Catalytic [2+2+2] Cycloaddition Reactions

      Yasushi Satoh and Yasushi Obora

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500358

      Thumbnail image of graphical abstract

      Niobium can exist in a number of different oxidation states (from +5 to –3), and it is anticipated that Nb complexes should possess unique reactivity in organic transformations. Previously, low-valent niobium complexes were used as reagents in organic reactions. In recent decades they have been used as catalysts in various [2+2+2] cycloadditions.

  33. Full Papers

    1. Artemisinin Model Systems

      Model Studies on Peroxidic Glutathione Transferase (GST) Inhibitors: C5-Methylated 1,2,4-Trioxanes with C6-Acrylate Side Chains

      Axel G. Griesbeck, Andreas Maaßen, Maria Bräutigam and Markus Pietsch

      Article first published online: 29 APR 2015 | DOI: 10.1002/ejoc.201500326

      Thumbnail image of graphical abstract

      A route to 5-methylated 1,2,4-trioxane acrylates is described. These compounds show moderate inhibition of glutathione transferase (GST).

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